HETEROCYCLIC BETAINES .14. (E)-1-ALKYL-[2-(IMIDAZOL-2-YLIDENE)ETHYLIDENE]DIHYDROPYRIDINES WITH A BETAINE CHARACTER - AN IMPROVED PROTOCOL FOR A KNOEVENAGEL-TYPE CONDENSATION FOR SYNTHESIS OF (E)-1-ALKYL-[2-(1H-IMIDAZOL-2-YL)VINYL]PYRIDINIUM SALTS

被引：9

作者：

ALCALDE, E

ROCA, T

机构：

[1] Laboratorio de Quimica Orgánica, Facultad de Farmacia, Universidad de Barcelona

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 18期

关键词：

D O I：

10.1021/jo00044a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel class of aza analogues of (E)-stilbene, the (E)-1-alkyl-[2-(imidazol-2-ylidene)ethylidene]dihydropyridines 4A <-> 4B, 5A <-> 5B, have been studied. They were synthesized by a convenient two-steps procedure. In each of the steps, the necessary basic reaction medium has been generated by a strong basic ion-exchange resin (OH- form). Thus, a modified protocol of the Knoevenagel condensation has been applied to preparation of the title (imidazolylvinyl)pyridinium salts, deprotonation of which yields several examples of compounds 4 and 5. The betaine character of 4 and 5 is well reflected by their physicochemical properties and reactivity toward electrophiles (Mel).

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页码：4834 / 4838

页数：5

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